


Flying High

by SongbirdAli



Series: Flying High [1]
Category: Supernatural
Genre: Airplane Romance, Blow Jobs, Bunker Fluff, Bunker Sex, Cunnilingus, Curvy Girl, F/M, Fluff, Insecure OFC, Lovey-Dovey, Men of Letters Bunker, Oral Sex, Reassuring Sam Winchester, Romance, Smart Sam Winchester, Smut, Vaginal Sex, thick thighs
Language: English
Status: Completed
Published: 2018-07-15
Updated: 2018-09-20
Packaged: 2019-06-10 15:15:13
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 5,257
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15294255
Author URL: https://archiveofourown.org/users/SongbirdAli/pseuds/SongbirdAli
Summary: Sam is ready for a long nap on his flight home but his seatmate draws all of his attention.  He finds himself falling hard for a girl he hardly knows.  Just how far will he go to keep her close?





	1. Flying High

**Author's Note:**

> I'm going for curvy girl appreciation here but this is the first time I've written it so please give feedback, it's absolutely welcome. Sam is such a tender soul, I really felt that he was the best match for our OFC. All bodies are beautiful and Sam gets that in a way our sweet, albeit insecure, Hailey doesn't yet. Maybe Sam can show her just how beautiful she really is. <3

It's been a long trip.  Sam was exhausted and looking forward to a long nap as he boarded the plane.  He picked the seat by the emergency door so he'd have some extra leg room.  He'd been almost a head taller than everyone else since midway through high school and it was a blessing and a curse.   With a weary smile to the stewardess as he carried his heavy bag down the ramp. She blushed and smiled back at him when he ducked through the opening into the main cabin.

"Welcome aboard!  Can I get you anything before you're seated, um..."

"Sam, and nah, I'm good I think." Sam moved quickly past her to get to his seat.  The overhead bins were all open so he shoved his duffel into the one above his row and swung himself into the aisle seat.  He'd wanted the window seat when he booked but someone else had already purchased it.  He was hopeful that they weren't a talker.  Sleep was calling his name but he didn't want to be rude and make someone wake him up to get into their seat.

His eye caught on an attractive woman making her way down the aisle with a bulky backpack.  Her dark hair was drawn up into a messy bun, little tendrils of hair spilling from the sides.  She looked as though she was just as tired as he was.  With a book shoved between her arm, and the side of her ample breast, and a pair of glasses perched on her nose threatening to fall, she stopped in front of him and struggled to push her bag into the compartment above her head. 

"Hey, uh, can I give you a hand?" Sam spoke to the bare midriff in front of his face.  As if she had just noticed it had been lifting her t-shirt a little too high, she dropped the bag and grabbed at her shirt.  Sam caught it and chuckled as her cheeks blushed crimson.

She adjusted her glasses as she apologized. "I'm so, so sorry.  This stupid bag is going to be the death of me.  That's the last time I try to get all my stuff into a carry on.  Thank you so much."

Her eyes followed him as he stood, mouth dropping open in shock.  Sam was long and lean and his muscle stretched against the soft cotton of his shirt. Her eyes were stalled on a small strip of his exposed midriff when he spoke.

"Are you my seatmate?"  He grinned at her when she finally looked up to meet his warm hazel eyes.  She was mortified and nodded before seating herself quickly.

He climbed back into his seat and teased her as he buckled his seat belt.  "It's only fair, you did give me a show first."

"Oh my god, I'm so embarrassed. I swear I don't expose myself to everyone I meet.  I'm Hailey, and you are?"

"Sam Winchester.  It's nice to meet you.  Is Kansas home, or are you just going to be passing through?"  Sam wasn't so tired all of a sudden.  This sweet creature had his full attention.

"Oh, Kansas is home.  I was born and raised in Lebanon.  You?"  She brushed the hair from her forehead and smiled at him as his face gave away his surprise.

"Lebanon is home for me too.  At least it is now.  We've been all over the place.  Small world!"  Her face fell just slightly at his words.  His heart sank thinking maybe he'd scared her off with his enthusiasm.

"We, huh?  So are you married then?"  She smiled softly and looked down at the cover of her book as she kicked off her shoes and settled in.  Sam watched her profile and wondered what her hair looked like released from the confines of the hair sticks holding it in place.

"I'm sorry, what?" 

"You said, 'we', are you married?"  She began to wish she hadn't asked and felt like she was prying.

"OH! No, no.  I meant my brother.  We live together.  Sorry, I should have been more clear. What about you?  Is there someone special?" He tucked his long, auburn hair behind his ear when he spoke, she couldn't take her eyes off of the way his fingers moved and the fluid ripple of his forearm.

"Who, me?  Ha, no.  Not anyone at all for a long time, actually."  She went back to studying the cover of her book nervously, the intensity of the look in his eyes made her feel exposed.  This guy was way out of her league and just being friendly.  She was obviously reading into things and embarrassing herself. Nervously she pulled off her glasses and tucked them into her hair.

"That's surprising, someone like...I mean, you're" Sam cleared his throat anxiously, "sorry, apparently I've forgotten how to flirt without being creepy."  Sam shifted uncomfortably in his seat and adjusted the legs of his jeans.

She laughed a little too loudly, "Flirt?  With me?  Come on.  My nose is usually shoved in a book.  It's been so long, I don't think I'd know flirtation if it slapped me across the face."

"Well I'm definitely not going to do that." They smiled at each other just a little longer than they should before Sam squirmed and readjusted in his seat.  He was cramped even with the extra leg room.

"You look pretty uncomfortable.  I've got extra room, I mean, your legs are a lot longer than mine.  You could sit angled this direction and use the whole length of the row."  She blushed again and he couldn't help but give a wide grin exposing his dimples.  She almost melted on the spot.

"Are you sure you want me invading your space?"  He smirked at her and her breath caught in her throat.  

"I offered, didn't I?" She didn't know where that confidence came from but it was working for her.  She crossed her legs toward him, opening up more space in front of her.  Sam angled his backside toward the aisle and stretched his legs toward the window, crossing his large boots at the ankle.  Hailey took a chance and tucked the socked toes of her crossed leg under his hard calf, pinning her legs in place so she could relax her thighs.  "See, now we both win." She quipped and turned to grin at him, proud of how she'd worked this to her advantage.  Now she got to touch him for the whole rest of the flight.  

"You have beautiful eyes, Hailey." He seemed more shy all of a sudden and it just made him more attractive.  The stewardess had pulled up with the drink cart just as the words left his mouth.  She grinned and echoed his sentiment. "You really do, honey.  Now, take a look at the drinks we have for you and let me know what you'd like."  They all laughed and Sam collected their drinks as Hailey dropped open their trays.  "You two are really cute together." she said before she moved on to the next row.

Sam pushed a misbehaving piece of hair out of Hailey's eye as he spoke, "Maybe she's on to something..."

You toyed with the hem of your shirt before quietly responding, "Maybe..."

"Tell me about the book you're reading.  What's it about?" he wanted to know everything about her.  

For the rest of the flight they talked comfortably about everything and anything.  She was obsessed with the paranormal and he loved the way her eyes lit up when she talked.  She was impressed with his seemingly endless knowledge on the subject, and the span of those shoulders.  Before they knew it the plane was preparing to land.  This was the part Hailey hated the most.  There was something about the sinking feeling of the dropping altitude and the shriek of the tires that scared her to the point of freak out.  Sam noticed her white knuckling the arm rest and immediately wanted to comfort her.

"Hey, you ok?" he pulled his legs back to his side of the row and covered her her hand with his as he leaned closer to her.  Hailey nodded but gritted her teeth against the quaking in her gut. "No you're not.  Give me your hand, let me help."   Hailey snaked her arm behind his and grabbed on to his arm, burying her face in his bicep.  Sam smiled softly as he stroked her cheek and whispered to her that everything was going to be just fine.

When the tires finally hit the tarmac Hailey gasped and dug into his arm. "OW OW OW...OK, ok...we're down.  It's fine." he chuckled as her grip released but kept her hand tight on his arm until they had stopped.  She looked up at him and mouthed a heart-felt "Thank you".  Sam brushed his nose against hers and leaned slowly in for a kiss.  Reaching up to cup her cheek with his large palm, he took her bottom lip into his mouth.  Hailey released his arm and pushed her hand up into his hair, her mind a whirl wishing they were anywhere but in a plane full of people.

Overhead compartments were popping open all over the plane but they were blind to the knowing glances and rolling eyes as their fellow passengers strolled past. All that mattered was the feel of his warm thumb on her cheek and the softness of his lips.

When he finally pulled away, he rested his forehead on hers and drew a long breath. "Hailey, I don't usually kiss virtual strangers on planes but I would really like to do that again sometime."

"Me too." she answered before nervously worrying her lip with her teeth

He kissed her forehead before standing up to grab their bags.  He threw on her backpack with ease and grabbed his duffel before reaching for her hand.  

"You didn't have to make it look THAT easy" she joked, pointing to the backpack.  

"You'd be surprised how much I can lift." he said with a wink.  Her cheeks burned and her insides turned to goo.  This can't possibly get any better. 

"My car is in the long term parking.  Need a lift home?" She asked while they were walking down the aisle toward the still beaming stewardess.

"Oh hell yes." he joked over his shoulder, still holding tightly to her hand.

The stewardess stepped out of the way as they moved past and called up the ramp "Have a good night, you two!"

 


	2. Do you see what I see?

Sam followed behind Hailey as she hunted down her car in the Airport Parking. He couldn't keep from stealing occasional glances at her rounded bottom and chastised himself for being so shallow. She was beautiful, sure, but also smart and funny. He was already trying to figure out how to keep her around and he couldn't remember the last time he'd been that gone so quickly.

Hailey wandered between cars, desperately trying to remember where she'd parked. At a little over 5 feet tall, she had a tough time seeing over the rows of cars to pinpoint her own in the crowd. In a stroke of genius, she pulled her keys out of her purse and hit the lock button. Lights flashed down the row to their left and Sam took off like a shot, running backward and laughing at her shocked expression. She watched him trot with a smirk on her lips wondering how she'd found this dopey puppy of a man.

When he reached the trunk, she punched a button on the fob to open the trunk just as Sam bent to put the bags down. The trunk popped open and hit him in the forehead with a thud. He grabbed his head and bent in half with a groan. Hailey ran to close the distance between them, apologizing all over herself.

"Oh god, I'm so sorry! Are you ok?!" Her fingers slid into the back of his hair and just for a second she was mesmerized by how soft it was. He grinned sheepishly as he rubbed his face, a blush creeping across his cheeks and neck.

"I'm good, just feeling like an idiot. Are you going to let me in the car or make me ride in the trunk since you don't really know me?" He flashed his dimples and she melted.

"Get in the car, Sam Winchester, _if_ that's your real name." He laughed and climbed into the passenger seat as she started the car and began the hour and a half journey back to Lebanon.

* * *

 

Sam watched her out of the corner of his eye while she drove, his mind raced thinking of ways to see her again. This drive just wast going to cut it. She  was trying not to be self-conscious about a possible double chinned profile, and how her body looked in this t-shirt that hid nothing.  When she got ready this morning she wasn't thinking about sitting next to some ridiculously hot guy on an airplane. He smiled as she fidgeted and looked uncomfortable and couldn't help but to tease her a bit.

"You look nervous. Do you not usually pick up strange men on planes?" She relaxed slightly and turned her head quickly to give him a playful scowl.

"How dare you sir, you picked ME up. You kissed me, remember?" Sam laughed easily and feigned shock.

"Hails, you grabbed onto me for dear life, I feel like I've been suckered." Hailey giggled like a teenager and quickly covered her mouth to stop it. He immediately tugged at her arm.

"You have the most adorable giggle I've ever heard! Why would you cover that up?!" Embarrassed, she brushed the compliment off, as she did all compliments.

"It's childish. I've been trying to keep from doing it since I was young but just can't keep it together." She shrugged as she spoke, and tried to push down the memories of cruel teenage boys mocking her.  
"Wanna listen to some music? You can pick anything you like."

Sensing she needed to change the subject Sam popped on the radio and began station hopping, settling on soft rock. He wasn't looking for a romantic gesture but it wouldn't hurt to have some love songs playing, right?  Dean was an endless supply of hair band rock, this was a welcome break.

  
He took her left hand in his palm, tracing the backside with a finger tip from his right, marveling at how small it was. Goosebumps broke out over her arms as she put the car on cruise and enjoyed the feeling of his warmth against her fingers. They were comfortable in the silence. No one needed to talk, though there was much to ask. They just relaxed into the feeling of being close for now. 

Before they knew it Hailey was pulling up in front of the bunker. She shot Sam a questioning glance. "You're one of the weirdos that live here?"

"Weirdos?? Is that what they call us in town?" Sam laughed uncomfortably. She'd heard about them. He thought they'd kept a reasonably low profile but apparently not.

"Yeah well, you let me drive you home so maybe you are a little weird." She smiled at him nervously and opened the car door to get out. Sam pushed open his door and met her behind the car. They stood there awkwardly for a second before Sam decided to take matters into his own hands.

"Can I hug you? I probably should have asked before I kissed you but I got swept into the moment, I think. I'm not usually such a cave man." He looked so dreamy and nervous, his eyes roaming over her face like a hopeful kid. She grinned and wrapped her arms around him, looking up into his face.

"Just kiss me already. I'm not usually so easy but you had me at cave man." he chuckled and shocked her when he picked her up and sat her on the trunk, bringing her face much closer to his own. His palms cupped her cheeks as his thumbs stroked her face. They stayed that way for what felt like a delicious eternity before he wet his lips and leaned in. The heat of his breath was amplified in the cold night air. He took her bottom lip between his own soft ones and pulled gently with his teeth. She couldn't help but whimper against him. A hot flush crept over her skin as she wrapped her legs around him and pulled him closer. Sam allowed himself to be led and slipped his fingers into her thick hair, letting his tongue glide whisper soft against her lip. Pulling her auburn waves gently, he coaxed her head back so he could nose into her neck behind her ear. She smelled of flowers and rain and made his body light up with need. He kissed down her neck and into her shoulder, apologizing as he went.

"I'm sorry...I can't...seem to stop...should I?" The tip of his tongue trailed lazy circles at the corner of her neck and shoulder as she trembled and moaned softly.

"Don't you dare." she whispered.  Her whole being was aglow with the promise of release. Sensations she hadn't felt in years brought her body back to life in ways she'd forgotten existed.

Slipping her hands into the back pockets of his jeans, she pulled him in until his need was rubbing up against her.  He groaned as his teeth pulled at her earlobe.  Taking a deep breath, he pulled back and caught her blue eyes with his hazel ones.

"How wrong is it for me to ask someone I just met to come inside?  I really want to give you a tour of my bedroom right now." He smirked as she bit into her lip to stifle a whimper.  A nod was all she could muster so without so much as a thought to grabbing the bags, he slid his arms under her full thighs, lifted her into his arms, and headed for the bunker. 

Hailey slipped her arms around his neck and nibbled at the scruff at his jaw while wrapping her legs around his waist.  The rumble in his chest as he hurried to the door brought a wicked grin to her face.  Combing through his hair, she ran the tip of her tongue up his neck to his ear.

"You know, you could give me a tour of more than the bedroom." her soft, warm whisper in his ear pulled a low growl from his gut and he quickened his pace as he popped open the door and hurried down the stairs.  

Dean jumped up from his seat at the table in the Library as Sam barreled onto the stairs.  When it registered that his little brother was home with a woman literally wrapped around him, a proud grin spread across his face.  

"Well hello Sammy..." he laughed as he dropped back into his chair and went back to his research while taking a long draw from his beer.  Sam stopped and spun to face Dean as he stepped off the stairs, suddenly very aware that he wasn't the only one home.  Hailey buried her embarrassment into his neck and tried not to think about how this looked.  

"Uh, Dean....Hailey, Hailey....my brother Dean." Before Dean could respond, Sam turned and headed for his room while whispering an apology into her ear, chuckling at the ridiculousness of the situation.  Thankful that his door was already open, he stepped inside and kicked it closed.

Setting her down gently on the bed, he took a step back to look at her and catch his breath.  Dean's presence had interrupted the heat wave they were both riding and he wanted to slow down and enjoy this.  His eyes roaming over her brought all the self-consciousness that she'd forgotten moments ago right back to the surface.  Her cheeks flamed red and her arms folded awkwardly across her middle to hide what she saw as a flaw.  Sam didn't see anything but her, beautiful and soft and waiting just for him.   How did this even happen?

Dropping down onto the bed next to her, he took her hand in his and stroked the back of it with his thumb in an effort to bring her back from wherever she was in her head.  

"Are you ok? Obviously, I want this but I feel like I've lost you somewhere." His eyes showed his concern that maybe he'd pushed too hard to fast.  One night stands weren't his thing and he knew that's what this looked like.

"Yeah, I just don't usually do this.  It's not like I have all kinds of opportunities but..." she laughed nervously and he finally started to pick up on the little clues she'd been giving him all day.

"Hailey, when I look at you I see a beautiful woman.  Sure, I was attracted to you from the moment I saw you trying to carry that backpack down the aisle of the plane and even after you dropped that hundred pound thing onto me" she smirked at the memory while he continued "but then you grabbed me with your nervous smile and your intelligence, passion, and humor."  He ran a hand through his hair and grinned like a hopeful teenager, "I like you.  A lot.  So if you don't want to do this, we don't have to, but I want to see you again."

She smiled softly and leaned into his shoulder as she spoke, "I'd like that. I've just never experienced anything like this or anyone quite like you, so it makes me....nervous."

"We'll just go slow and if you want me to stop, I'll stop, but you have absolutely nothing to worry about.  I'm already in over my head." His long arms wrapped around her as she turned to press her lips to his. Her intention was to slow down but that familiar ember was catching fire again in her gut.  Just the smell of this man made her crazy.  She wasn't alone in her need, Sam had every intention of following her lead so when her kisses heated up and pulled at him rather than keeping him at a safe distance, he gladly charged in with his own desire. 

Turning to face her, he slid one hand behind her neck and the other under her left knee to pull her across his lap.  Once settled, he cupped her face in his hands and broke their kiss. She groaned her disapproval at the interruption.  Dropping an apologetic kiss on the tip of her nose, he leaned back slightly and pulled his t-shirt off, tossing it onto the floor.  Hailey's eyes and fingers explored his shoulders and chest as if she'd never seen a half naked man before.  She knew he was strong but she hadn't been prepared for the ripple of those muscles in action.

Sam's head cocked to the side as he grinned at her in expectation. He leaned back onto his hands and waited while she let her hands roam over him, relishing the touch of her soft fingers.  Hailey bit her lip nervously as she pulled her own shirt off and dropped it with his on the floor. Her breasts fell heavy with the motion, barely hidden behind a very thin, lacy bra.  Thank god she'd worn her best bra.  He licked his lips like a ravenous animal without even thinking.  The warm honey hue of her nipples peaked through the sheer lace and it was all he could do not to rip the fabric away from them.  Leaning forward he slid his hands up her back and over her shoulders as his lips and tongue explored her newly uncovered skin.  Breathing her in, he kissed over her shoulder and down onto her breast, letting his hot breath hover over her covered nipple.  It hardened in anticipation so he licked at it playfully drawing a whimper from her as she pulled at his silky hair.  That was all the agreement he needed.  Making short work of the clasp on her back, he flung the offending undergarment to the chair by the window and cupped her full breasts in his hands.  His kisses eagerly moved from one breast to the next until he could no longer resist the urge to pull her close. His arms wrapped around her again as his lips found her own.  He lay back on the bed, pulling her down with him, before letting his fingers trail down her back and onto her round ass.  He squeezed with a groan and rolled his hips up against her.

Hailey shuddered as her body begged for his touch.  She could feel the heat between her thighs and the hard press of him where she sat on his lap.  A rush of power burned through her with the realization that she was doing this to him.  Sitting up on his lap, she began to roll her hips slowly, teasing him with just enough friction to keep his fire burning if not cause an explosion.  He tilted his hips up just slightly and dug his fingers into her thighs as he tried to fight the urge to toss her back onto the bed and make her his.  Closing his eyes against the view to keep from blowing it too soon, he reached down to unbuckle his belt before her hands swatted his away with a laugh.  His eyes popped open in surprise as she giggled and began opening his jeans.  Sliding back off of him to stand at the foot of the bed, she bent to pull his pants and boxer briefs down and off his feet.  His cock lay against the soft trail of fur that led from his belly button to her target.   He smiled nervously as she took a deep breath and began unbuttoning her own pants.  Sliding them over her hips, she let them fall the rest of the way to the floor before stepping out of them and kicking them aside.  He groaned his approval and goosebumps broke out over her skin.

"If you like those panties you should probably take them off now because if I get my hands on them they're going to be ripped from you." The look on his face when he said it told her he wasn't kidding so she slid them over her hips and let them fall.  His eyes went wide as he beckoned her closer with an upturned finger.  Pulling her hair over her shoulder and out of the way, she crawled up the bed between his thighs, nibbling on them as she headed for his hard length.  The flat of her tongue drug up the underside of his cock, warm and wet.  Sam let loose with an expletive and leaned forward to take her hair into his hands.  It had been years since anyone had rained down this kind of pleasure on him and he wanted to take it all in.

She drug her full breasts over his length and watched his expression change from one of hopeful desire to one of desperation.  Her fingers wrapped around his length as she stroked against it's length, the throb she felt against her hand traveled straight to her depths.  Eyes locking with his, she lowered her mouth over his length and allowed her lips to close around his cock while her tongue teased and stroked against he underside.  Sam groaned and shook, fighting the urge to roll his hips again.

"Fuck, Hailey, I..." the words ground out between gritted teeth.  She worked him over in every way she could think of, thoroughly enjoying the control and the velvet feel of his skin in her mouth. Sam knew he couldn't take much more so he pulled gently on her hair, signaling her to stop.  Looking up at him with a soft smile on her lips, she drug the tip of her tongue over the cleft of his tip and stroked him slowly.

"Come here." His words were more command than request.  Hailey shuddered, and crawled over his body as he moved his hands down over her hips to pull her further forward until she was sitting on his chest.  Twisting to his left, he pinned her back onto the bed and began kissing down her soft belly.  Urgent kisses that gave away his unchecked desire and tiny nips that brought surprised gasps from his muse. Finally he hovered over her sex, his very tip of his tongue teasing her outer lips, before dipping inside to trail softly along the side of her nub.  She shuddered and tried to stifle her own moans as her body betrayed her desire to stay in control.  His warm tongue swirled around her rapidly swelling button before he spoke.

"Jesus, you taste good." Returning to her depths, he hooked his hands around the outside of her thighs and pulled her closer.  Biting her lip to keep quiet, she pushed one hand into his hair and grabbed a fistful of the sheets.  Sam was having none of it.

"Give in....give it to me" He groaned against her, letting his voice vibrate against her as his hands slid under her ass and lifted her closer as his tongue exacted it's revenge, working her closer and closer to release.  Hailey trembled beneath him before finally losing her grip.  She whimpered in desperation and found her own breasts with shaking hands.

"Don't stop Sam, don't....oh god..." her hips bucked up as her release hit before she could stop.  He chuckled as he brought her slowly down with gentle strokes and soft hums.  Her hands brushed the hair from his face as he looked up at her, eyes wide in wonder.  Sam lay his cheek against her warm thigh and sighed.

"You're so beautiful, Hails."  His left hand slipped up her abdomen and reached for hers, a tender gesture she didn't expect but so desperately wanted.  She looked into his eyes as her body slowly relaxed, amazed by this gentle giant who made her feel things she'd forgotten.

"Sam, I want to feel you....please." her soft begging was all he needed.  He moved over her aligning their hips before kissing her lips gently, a question as much as a promise.  Lifting her knees, she stroked her calves down his back before pressing into his hips with her heels.  "Please Sam...."

"Whatever you want, it's yours."  He breathed the words into her neck before slowly pushing into her.  Their desperate bodies hummed with the desire that had been threatening to boil over since they met.  Hungry kisses muffled moans and whimpers as the world shrank back to the size of his room.  Nothing mattered but the feel of his skin under her fingers, the stretch of her body around him, and the look in his eye as his body dropped over the edge of desire.  

Sam collapsed onto the bed beside her and pulled her body close to his, grateful kisses peppering her skin wherever he was close enough to reach.  She reached up and brushed the damp strands of his hair out of his face and behind his ear as he drew her in for a lingering kiss.  A kiss that promised of more to come.  One that begged her to stay.  Her legs intertwined with his in a silent response as she nestled into his neck for as long as he'd have her.

 

 

 

**Notes for the Chapter:**

> At this time, the story ends here. If you are interested in seeing where these characters will go, leave a comment and let me know! As always, thank you for reading and leaving a kudos or a comment. It really makes the effort worth it.
> 
> You are appreciated!


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